At their basic level, shoes protect one's feet, but they have become a way of indicating cool for a long time, starting with Converse, then moving to Puma and Adidas, a few other brands for a short time, and then to Nike. (There are more extensive histories, but this is a basic narrative.) So what to make of the new, very cool Obama shoes by Van?
The stunning shoes that Van produces are not very practical, in that shoes are close to the ground and can get dirty thus damaging the art. They are also less visible than let's say a t-shirt. But they reference a number of important trends. For one, they show the way Obama has become part of popular culture. Go to Van's site and you will see not only the Obama shoes, but all kinds of illustrated shoes, from a variety of cultural subjects including Spiderman, Tinker Bell, San Francisco, and Darfur. That Obama has joined these ranks itself shoes, er, shows the transformative nature of the campaign and the candidate.
Though Obama is probably the first national candidate to play basketball at this stage of his life, I think it's less about the shoes say less about this than about the cultural impact described above. Basketball shoes have gone way beyond sports; this semi-Obamian is in Europe, and in his country, he has seen many, many different kinds of Chuck Taylors here, in a population where almost no one plays basketball. To wear the Obama shoes--or to link to it on your website, which is more likely--is to show loyalty to Obama but also to show one's cool. In that sense, it's less about the shoes and Obama himself and more about the wearer.